Muñoz-Ramírez Alejandra, Mascayano-Collado Carolina, Barriga Andrés, Echeverría Javier, Urzúa Alejandro
Departamento de Ciencias del Ambiente, Facultad de Química y Biología, Universidad de Santiago, Santiago, Chile.
Unidad de Espectrometría de Masas-CEPEDEQ Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile.
Front Pharmacol. 2020 Nov 30;11:594257. doi: 10.3389/fphar.2020.594257. eCollection 2020.
(Molina) Hook. and Arn. (Anacardiaceae), common name Litre, is an evergreen endemic plant used in the Mapuche Chilean folk medicine. The stem juice of mixed with (blackberry) is used to treat cough and the infusion of leaves is used in baths to treat joint inflammations. In this study, the activities of 3-n-alk(en)yl-catechols, obtained from the dichloromethane extract of the epicuticular compounds of fresh leaves (DCME), stem bark petroleum ether extract (PEE), fractions of phenols and phenol-acid compounds obtained from the methanolic extract (methanolic extract) of defatted leaves and aqueous infusion (AE) from fresh leaves, were evaluated as inhibitors of soybean 15-lipoxygenase (15-sLOX) and human 5-lipoxygenase (5-hLOX), one of the inflammation pathways. The 3-n-alk(en)yl-catechols were characterized by gas chromatography-mass spectrometry and 1D and 2D nuclear magnetic resonance analysis as mixtures of 3-[(10E)-pentadec-10'-en-1-yl]-catechol, 3-[(10Z)-pentadec-10'-en-1-yl]-catechol and 3-n-pentadecylcatechol. In addition, two fractions, obtained from MeOHE, were characterized by liquid chromatography electrospray ionization tandem mass spectrometric as complex mixtures of known acids and phenolic compounds. DCME, MeOHE and ethyl acetate extract (AcOEtE) extracts showed inhibition against 15-sLOX, and the AE of fresh leaves, showed the best inhibition against 5-hLOX. The mixture of 3-n-alk(en)yl-catechols showed inhibition of 15-sLOX and 5-hLOX. The compounds 3-[(10Z)-pentadec-10'-en-1-yl]-catechol (IC 2.09 µM) and 3-n-pentadecylcatechol (IC 2.74 µM) showed inhibition against 5-hLOX. The inhibition values obtained for the 3-n-alk(en)yl-catechols are in the range of well-known inhibitors of 5-hLOX. Acetylation of the 3-n-alk(en)yl-catechols blocks the inhibitory activity, indicating that the free catechol function is necessary for the enzyme inhibition. In addition, the fractions of phenols and phenol-acid compounds showed inhibitory activity against 15-sLOX and the AE, showed a good inhibition against 5-hLOX. These results would be in agreement with the use of , as an anti-inflammatory in Mapuche ethnomedicine.
莫利纳钩枝藤（Molina）和阿诺特钩枝藤（Hook. and Arn.）（漆树科），俗名利特雷（Litre），是一种智利马普切民间医学中使用的常绿本土植物。其茎汁与黑莓混合用于治疗咳嗽，叶的浸剂用于沐浴以治疗关节炎症。在本研究中，对从鲜叶表皮化合物的二氯甲烷提取物（DCME）、茎皮石油醚提取物（PEE）、脱脂叶甲醇提取物（甲醇提取物）中的酚类和酚酸化合物馏分以及鲜叶水浸剂（AE）中获得的3 - n - 烷（烯）基儿茶酚作为大豆15 - 脂氧合酶（15 - sLOX）和人类5 - 脂氧合酶（5 - hLOX）（炎症途径之一）的抑制剂的活性进行了评估。通过气相色谱 - 质谱联用以及一维和二维核磁共振分析对3 - n - 烷（烯）基儿茶酚进行表征，确定其为3 - [(10E) - 十五 - 10'- 烯 - 1 - 基] - 儿茶酚、3 - [(10Z) - 十五 - 10'- 烯 - 1 - 基] - 儿茶酚和3 - n - 十五烷基儿茶酚的混合物。此外，从甲醇提取物中获得的两个馏分通过液相色谱电喷雾电离串联质谱表征为已知酸和酚类化合物的复杂混合物。DCME、甲醇提取物和乙酸乙酯提取物（AcOEtE）对15 - sLOX有抑制作用，鲜叶的AE对5 - hLOX的抑制作用最佳。3 - n - 烷（烯）基儿茶酚混合物对15 - sLOX和5 - hLOX有抑制作用。化合物3 - [(10Z) - 十五 - 10'- 烯 - 1 - 基] - 儿茶酚（IC₅₀ 2.09 μM）和3 - n - 十五烷基儿茶酚（IC₅₀ 2.74 μM）对5 - hLOX有抑制作用。3 - n - 烷（烯）基儿茶酚获得的抑制值处于5 - hLOX已知抑制剂的范围内。3 - n - 烷（烯）基儿茶酚的乙酰化会阻断抑制活性，表明游离儿茶酚官能团对于酶抑制是必需的。此外，酚类和酚酸化合物馏分对15 - sLOX有抑制活性，AE对5 - hLOX有良好的抑制作用。这些结果与马普切民族医学中使用该植物作为抗炎药的情况相符。
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